Process for preparing fluorochemical monoisocyanates

• US 7,361,782 B2
• Filed: 07/12/2006
• Issued: 04/22/2008
• Est. Priority Date: 12/31/2003
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Moore, George G. I., Klun, Thomas P., Qiu, Zai-Ming, Clark, John C., Kirk, Alan R.
• Primary Examiner(s): Eyler; Yvonne
• Assistant Examiner(s): Katakam; Sudhakar
• Application Number:
  US11/457,037
• Publication Number:
  US 20060247460A1
• Time in Patent Office: 650 Days
• Field of Search: 560/330, 560/336, 560/27
• US Class Current: 560/330
• CPC Class Codes: C07C 303/40 by reactions not involving the formation of sulfonamide groups
• CPC Class Codes: C07C 311/09 the carbon skeleton being further substituted by at least two halogen atoms

Abstract

A process for preparing fluorochemical monoisocyanates comprises reacting at least one fluorochemical alcohol represented by the formula C_nF_2n+1SO₂NCH₃(CH₂)_mOH, wherein n=2 to 5, and m=2 to 4, with 4,4′-diphenylmethane diisocyanate (MDI) in a solvent in which the resulting fluorochemical monoisocyanate is not soluble; wherein the molar ratio of fluorochemical alcohol:MDI is from about 1:1 to about 1:2.5.

Claims

1. A fluorochemical isocyanate composition prepared by a process comprising reacting at least one fluorochemical alcohol represented by the formula C_nF_2n+1SO₂NCH₃(CH₂)_mOH, wherein n=4 and m=2 to 4, with 4,4′

-diphenylmethane diisocyanate (MDI) in a solvent having a solubility parameter of less than about 8.3 (cal/cm³)^1/2 and a hydrogen bonding index of less than about 4;

wherein the molar ratio of fluorochemical alcohol;

MDI is from about 1;

1 to about 1;

1.5; and

wherein said composition comprises greater than about 85% monoisocyanate.

2. The fluorochemical isocyanate composition of claim 1 wherein said composition comprises greater than about 90% monoisocyanate.

3. The fluorochemical isocyanate composition of claim 2 wherein said composition comprises greater than about 95% monoisocyanate.

4. The fluorochemical isocyanate composition of claim 1 wherein said fluorochemical alcohol is selected from the group consisting of C₄F₉SO₂NCH₃(CH₂)₂OH, C₄F₉SO₂NCH₃(CH₂)₄OH, and mixtures thereof.

5. The fluorochemical isocyanate composition of claim 4 wherein said fluorochemical alcohol is C₄F₉SO₂NCH₃(CH₂)₂OH.

6. The fluorochemical isocyanate composition of claim 1 wherein said solvent is a nonpolar solvent.

7. The fluorochemical isocyanate composition of claim 6 wherein said solvent is a non-aromatic hydrocarbon or halogenated solvent.

8. The fluorochemical isocyanate composition of claim 1 wherein said solvent is selected from the group consisting of methyl nonafluoroisobutyl ether, methyl nonafluorobutyl ether, petroleum ether, n-heptane, and mixtures thereof.

9. The fluorochemical isocyanate composition of claim 1 wherein said molar ratio of fluorochemical alcohol:

MDI is from about 1;

1 to about 1;

2.

10. The fluorochemical isocyanate composition of claim 9 wherein said molar ratio of fluorochemical alcohol:

MDL is from about 1;

1.1 to about 1;

1.5.

11. The fluorochemical isocyanate composition of claim 1 wherein said fluorochemical alcohol and said MDI are reacted in the presence of a catalyst.

12. The fluorochemical isocyanate composition of claim 11 wherein said catalyst is an organotin compound or a tertiary amine.

13. The fluorochemical isocyanate composition of claim 12 wherein said catalyst is dibutyltin dilaurate.

14. The fluorochemical isocyanate composition of claim 1 wherein the monoisocyanate is represented by the formula:

15. The fluorochemical isocyanate composition of claim 1 wherein the monoisocyanate is